4-Toluenesulfonyl chloride → HCID 15049040, compound

HRID 484552Notes

Reaction equation

HRID 484552 reaction equation
[Cl-].[C:2]([CH2:5][O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[NH3+:13])([OH:4])=[O:3].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>[OH-].[Na+].C(OCC)C>[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([NH:13][C@@H:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C@H:7]2[O:6][CH2:5][C:2]([OH:4])=[O:3])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 67747384HCID 67747384, compound

Product 1

HCID 15049040HCID 15049040, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of trans-2-carboxymethoxy-cyclohexyl ammonium chloride (1.048 g, 5 mmoles) in 1N NaOH (15 ml), there was aded a solution of p-toluenesulphonyl chloride (1.048 g, 5.5 mmoles) in diethyl ether (20 ml). The mixture was vigorously stirred for 20 hours at room temperature. The aqueous phase was separated, washed with diethyl ether (20 ml), acidified with HCl 18% to pH 2 and extracted with diethyl ether (5×20 ml). The organic extracts were dried with MgSO4, the drying agent was filtered off and filtrate was evaporated in vacuo. The residue was recrystallized from diisopropyl ether. Thus, there were obtained 1.09 g (67%) of the title compound in the form of white crystals, melting point 56°-58° C.

Workup

  1. customThe aqueous phase was separated
  2. washwashed with diethyl ether (20 ml)
  3. extractionextracted with diethyl ether (5×20 ml)
  4. dry with materialThe organic extracts were dried with MgSO4
  5. filtrationthe drying agent was filtered off
  6. customfiltrate was evaporated in vacuo
  7. customThe residue was recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-e31b0eab13a2408d804c572897a23672
Source dataset
uspto-grants-1993_07
Patent number
US05231216

Reaction notes

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